While I love stocking up on statement pieces as much as the next girl, nothing is more important to me in my closet than my quality basics. Over the years, my Gap pieces have never gone out of style and consistently carry me season to season. Whether it's a cozy lounge set, an oversize tote bag, or a classic rollneck sweater, Gap has captured a timeless aesthetic that can help you build out a complete wardrobe. If you find yourself shopping for back-to-school pieces or wanting to mix it up with trendier silhouettes, the Gap and Gap Factory fall offerings should be your first stop. Ahead, find the 12 items I have on my shopping wish list, from an adorable teddy bag charm to a chic cropped cardigan.
Happy Ugg season to all who celebrate. You and your feet made it through many long months of flip-flops, both wedge heeled and flat. It's now time to submerge them in sheepskin, just as Bella Hadid did in NYC this week. If you're wondering how to make the Ugg boots you already own look fresh, I highly suggest following Hadid's lead.
The boots Hadid chose were the Ugg Classic Ultra Mini Boots, a style that's retained its popularity since being released in 2020, and she made them look as fresh as ever, thanks to the outfit she wore upon arrival in the city. So what do you need to re-create the outfit to wear with Uggs now and into 2027? (Yes, it's that good.) Well, you might already own most of the classic pieces she opted for. For starters, Hadid wore a pair of straight-leg, high-rise blue jeans. On top was a collared bomber jacket in a neutral medium brown worn over a plaid button-down and graphic T-shirt. Of course, on her feet were the aforementioned Ugg boots with white socks. As for accessories, she chose oval sunglasses, a two-tone baseball cap, and what's sure to be the Coach It bag of fall 2026—the Alter/Ego Slouchy Shoulder Bag.
Yes, this is a lot of pieces, but in the interest of simplifying things, I'd say the main items are the bomber jacket, plaid shirt, and boots, and you're free to accessorize and layer as you see fit. If you'd like to re-create Hadid's look from head to toe, keep scrolling to shop everything you need, along with some of the trendiest Ugg boots on the market.
I'm Gen Z. My sister is a millennial. Growing up, I had a front-row seat to her fashion evolution. On Monday, it was Kimora Lee Simmons meets Devon Aoki, and by Friday, it resembled Kate Moss on the grounds of Glastonbury—muddy boots and all. When Gossip Girlpremiered, she outfitted herself as if she were a Fifth Avenue regular. Then came her twee era, my personal favorite. Zooey Deschanel and Alexa Chung were her icons and mine, too, by default. Nearly 10 years later, I still get phone calls with updates on her latest fashion endeavors.
While working in the industry, I've learned that my sister's inability to hone in on one singular aesthetic isn't unique to her. Vibe shifts are inevitable, and the last 20 years have proved just that. It just so happens to be Who What Wear's 20th anniversary, and after two decades of reporting on trend cycles and celebrity style, we're taking a moment to reflect on how far fashion has come since the aughts.
Ahead, read my retrospective of the 20 iconic fashion aesthetics that defined the past 20 years. Starting with McBling, I've drafted a timeline that spans embroidered Fendi Baguettes, the rebellion of indie sleaze, Peter Pan collars, the flower crowns of Coachella, and Tumblr 2014, making my way to the clean girls, chic Parisians, and vintage archivists who write the aesthetics of today. If you're interested in seeing the progression from "That's hot" to office siren, keep scrolling.
McBling
(Image credit: Getty Images)
The early-to-mid aughts were defined by glitz and glamour. Think Paris Hilton celebrating her 21st birthday, Sarah Jessica Parker and her embroidered Fendi Baguette, and Missy Elliott accepting a Grammy in a hot-pink velour tracksuit. Whether people were posing for paparazzi or hanging out at the mall, trucker hats, blinged-out miniskirts, wraparound shades, low-rise jeans, and bejeweled shoulder bags were the norm—just ask SJP.
Von Dutch
99' Rhinestone Tank
MANGO
Rhinestone Denim Miniskirt
fendi
Baguette 26424
Indie Sleaze
(Image credit: Getty Images)
There are only a handful of moments that define a fashion era. Chung and her then-boyfriend Alex Turner at the 2008 Glastonbury Music Festival is one of them. From the mid-aughts to the mid-2010s, there was a spike in hedonism. Music from artists like Arctic Monkeys and LCD Soundsystem and celebrity fashion of the time (e.g., Mary-Kate Olsen in a fur coat, skater skirt, and tights) embraced the maximalism of uncertainty and unregulated authenticity.
This aesthetic undoubtedly correlated with the premiere of Gossip Girl in 2007, and Serena van der Woodsen's and Blair Waldorf's wardrobes were largely responsible for the sudden interest in the East Coast elite. The quiet charm of the Upper East Side and the old money background likely contributed too. Rooted in academia and collegiate styling, pleated skirts, plaid suiting, and pussy-bow blouses became mainstream trends.
Veronica Beard
Miller Houndstooth Dickey Jacket
Sandro
Pleated Skort
Reformation
Ani Ruched Loafer
Twee
(Image credit: Getty Images; Shutterstock)
This was an era of peak millennial optimism. Streaming Camera Obscura, debating who's really at fault in 500 Days of Summer, watching Portlandia, wearing Peter Pan collars, saving Alexa Chung outfits on Pinterest, buying vinyls, and cutting bangs after seeing Marlo Thomas in That Girl—that was the twee experience. Falling under the indie umbrella, twee looked to the '60s for A-line and shift dress silhouettes, mingled with hipster-associated media, and flirted with the peril of indie sleaze.
Reformation
Silver Bell Bag
Miu Miu
Poplin Dress
Schutz
Dafne Leather Flat
Business Casual
(Image credit: Getty Images)
Let's talk about it. By it, I mean statement necklaces. This chunky accessory was a staple among business-casual dressers. Body-con skirts, colorful blazers, peplum blouses, and contrasting prints were equally as popular. While this trend largely lived in real life and on Pinterest boards (guilty as charged), celebrities like Kim Kardashian and Rihanna embraced the corporate-adjacent aesthetic.
BaubleBar
Jane Beaded Necklace
ZARA
Poplin Peplum Top
Posse
Alice Striped Miniskirt
Model Off Duty
(Image credit: Getty Images; Shutterstock)
To achieve the unbothered allure of an off-duty 2010s supermodel, you must appreciate skinny jeans. Gisele Bündchen, Rosie Huntington-Whiteley, and Winnie Harlow certainly do. The skintight denim paired with an equally fitted tank, attitude-fueled boots, and an unbothered air became the unspoken outfit formula for go-sees and casting callbacks, and as expected with the skinny-jeans resurgence (I have my reservations), It girls have once again returned to this trusted combo.
Almina Concept
U Neck Tank
AG
Farrah Skinny Jean
simkhai
Kayla Chelsea Boot
Festival
(Image credit: Getty Images; Alamy; )
It was Coachella 2012. Vanessa Hudgens wore a flower crown, stacked bangles, and a boho duster. Today, we recognize her as a founding figure of music-festival fashion, influencing each Coachella of the mid-2010s thereafter. The vibe was gladiator sandals, cutoff denim, crochet tops, pull-on boots, fringe belts, and teashades. It spread from the muddy ground to downtown L.A., where it died down… until a few years ago. Coachella outfit guides returned to this boho-chic styling, and images of Jasmine Tookes's and Alessandra Ambrosio's festival 'fits resurfaced.
Massimo Dutti
Floral Print Flowing Shirt
Anna Kosturova
Marianne Crochet Midi Skirt
Frye
Harness 12R
Tumblr Grunge
(Image credit: Getty Images; Alamy)
In the mid-2010s, Tumblr hit its zenith—2014 to be exact. It was a time when long-sleeve tops were flannel, jeans were ripped, and graphic tees revealed your favorite artist. Ultraviolence hit streaming platforms. Divergent was released intheaters. And new additions were made to the lexicon: Gwyneth Paltrow and Chris Martin's "conscious uncoupling" and John Travolta's unfortunate "Adele Dazeem." It was here that everyone found their niche, and esotericism reigned supreme.
MATTEAU
Checked Cotton-Flannel Shirt
Urban Outfitters
Vintage Metallica Graphic Tee
frame
The Grunge Hang Short
Normcore
(Image credit: Getty Images;)
There's no shame in being basic. That was my takeaway from a 2013 report by trend-forecasting company K-Hole, which coined the term "normcore." In direct contrast to the childhood mantra of "Just be yourself," normcore celebrates sameness. When the pressure to differentiate from your peers becomes too much, normcore is a breath of fresh air wrapped in a plain white T-shirt, a pair of modest blue jeans, and maybe an oversize blazer if you're feeling frisky.
When hiking attire leaves the trail, you get gorpcore. If you're unfamiliar, GORP stands for "good ol' raisins and peanuts," which confirms the granola rumors. It's utilitarian, performance-driven layering that blurs the lines between outdoor gear and streetwear. It's not designer labels that move the needle here. Rather, it's top-notch performance brands like Arc'teryx, The North Face, and Salomon. All the technical information can be daunting to a beginner, so start small. A pair of cargo pants, a windbreaker, and hiking shoes will do the trick.
Prioritizing self-care, the end of 2021 marked the beginning of the clean girl era. You can recognize this aesthetic by its no-makeup makeup, matching workout sets, six-step skincare routines, prioritized cuticle health, and absence of split ends. Laura Harrier's and Hailey Bieber's street style are the paradigm—simple silhouettes and minimal makeup that let one's natural beauty shine.
Diane Keaton in Nancy Meyers's Something's Gotta Give—or, truthfully, any leading lady in the Meyers universe—and Martha Stewart are the epitome of this windswept, linen-wearing lifestyle. With roots along the East Coast, it predates its 2022 discovery coined by TikToker Lex Nicoleta. In contrast to its laid-back appearance, the coastal grandmother aesthetic takes a lot of effort to look effortless. Everything is hand-selected, from her woven tote to her Bermuda shorts.
This aesthetic is also described as balletcore, depending on where you fall on the "lover girl" spectrum. There's a good chance Black Swan is in your Letterboxd top four, Lana Del Rey is your most-listened-to artist, and you have a soft spot for the lace-trim trend currently sweeping FYPs everywhere. While coquette precedes balletcore, the two often go hand in hand. Ballet flats, leg warmers, ribbons, bows, pastel colors, and ruffles unify the two.
Likely linked to the rising popularity of Copenhagen Fashion Week, Scandinavian street style is characterized by its boxy, oversize silhouettes; unexpected color combinations; contrasting textures; and eye-catching footwear. They're the first to style the more controversial trends—ahem, balloon trousers, scarf belts, and capris—and you can always count on the Scandi style set for unpredictable pairings, like polka dot on polka dot.
Quiet luxury is the ultimate lesson in "less is more." It's quality over quantity. It's logoless brands. It's subtle signaling. Consider the correct buy-in (a The Row trench coat or Khaite trousers) a homing device for fashion insiders. Invest in basics, build a capsule wardrobe, and rely on the classics. Don't mistake this for uniformity; personal style is still appreciated.
You know the sportif aesthetic is done well when you're presented with two pieces that, on paper, should never go together, like running shorts and dainty kitten heels, but surprisingly complement each other. It's the juxtaposition that makes this casual athleticwear so enticing, and Bella Hadid knows it all too well. She was previously spotted in a rugby polo, a plaid midi skirt, and Adidas Sambas.
Despite the London address on her birth certificate, Jane Birkin set the standard for the Parisian aesthetic. Her lessons in laissez-faire dressing continue to dictate the wardrobes of modern French women—basket bags, lived-in denim, tailored blazers, and crisp button-downs. Of course, the grip that the color red has on Francophiles should also be mentioned. There's the red lip, Jeanne Damas's ruby pumps, and Audrey Hepburn wearing a scarlet gown on the steps of the Louvre in Funny Face.
Calling on the corporate attire of the '90s and early aughts, the office siren archetype is Gen Z's way of romanticizing the inevitable 9-to-5. Instead of rose-colored lenses, it's a pair of Bayonetta glasses. Despite their corporate origins, the trends that define this aesthetic are oddly not office-appropriate. Low-V-neck tops, cinched button-downs, ultra-miniskirts, low-rise trousers… The list goes on. Icons like Gabbriette Bechtel, Gisele Bündchen in The Devil Wears Prada, and Hadid stick to a muted grayscale color palette that evokes the mundanity of the corporate life cycle.
From Carolyn Bessette Kennedy to Sade, the '90s influence on contemporary dressing is undeniable. You can chalk it up to the streaming platforms and their role in this revival (looking at you, FX's Love Story), but Gen Z's nostalgia-driven anemoia is partly to blame as well. What makes this aesthetic so pleasing to the eye isn't just the limited color palette. It's also its unclutteredness. Jewelry is few and far between, logos are hidden, and silhouettes are uncomplicated.
This one's for all my vintage lovers out there. Your closet resembles a cabinet of curiosities: fringed shawls, artisan pillbox hats, Bianca Jagger–inspired slips, storied leather goods. Your affection for secondhand shopping doesn't limit you from buying new, but these new pieces must be worth conserving for future fashion historians like you. A look that lives rent-free in my mind? Paloma Elsesser in a Margiela F/W 97 dress-form tunic. On the new-in side, a Fendi Re Edition Baguette is a valuable addition.
fendi
Baguette 26424
dôen
Marcelle Midi Dress
Maison Margiela
Pink Tabi Satin Ballerina Heels
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